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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1622312Erstellt: 26. Oktober 2026

Cesium carbonate → 3-(1-Nitro-2-naphthylamino)benzonitrile

https://huagongshe.com/reaction/1622312

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktCesium carbonateHCID 10796—
Edukt2-Naphthylamine, 1-nitro-HCID 11823—
Edukt3-BromobenzonitrileHCID 23381—
EduktSodium BicarbonateHCID 516892—
EduktBinap, (A+-)-HCID 634876—
KatalysatorBis(dibenzylideneacetone)palladiumHCID 9811564—
Produkt3-(1-Nitro-2-naphthylamino)benzonitrileHCID 6799432337,4%

Reaktionsschritte

A solution of 1-nitro-2-naphthylamine (875 mg, 4.65 mmol), 3-bromobenzonitrile (846 mg, 4.65 mmol), cesium carbonate (3.03 g, 9.30 mmol), tris(dibenzylideneacetone)dipalladium(0) (213 mg, 0.23 mmol) and (+/−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (217 mg, 0.35 mmol) in toluenene (10 mL) was heated at 110° C. for 16 hours. The reaction mixture was poured into a saturated aqueous sodium bicarbonate solution, and was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1), to give the titled compound (503 mg, yield 37%).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08778933B2
Quelldatensatzuspto-grants-2014_07
ORD IDord-a99274e340834e36a7eb4c71349cc01e
Quellennotizuspto-grants-2014_07